DE2139212A1 - (Oxo-9 dihydro-6,9 4 H dioxino eckige Klammer auf 4,5-g eckige Klammer zu chinolyl-8)-carbonsäuren und ihre Isomeren - Google Patents
(Oxo-9 dihydro-6,9 4 H dioxino eckige Klammer auf 4,5-g eckige Klammer zu chinolyl-8)-carbonsäuren und ihre IsomerenInfo
- Publication number
- DE2139212A1 DE2139212A1 DE19712139212 DE2139212A DE2139212A1 DE 2139212 A1 DE2139212 A1 DE 2139212A1 DE 19712139212 DE19712139212 DE 19712139212 DE 2139212 A DE2139212 A DE 2139212A DE 2139212 A1 DE2139212 A1 DE 2139212A1
- Authority
- DE
- Germany
- Prior art keywords
- dioxino
- oxo
- dihydro
- quinolyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 25
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- -1 ethoxymethylene ethyl Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 231100000252 nontoxic Toxicity 0.000 claims description 11
- 230000003000 nontoxic effect Effects 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 7
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000020477 pH reduction Effects 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 238000005956 quaternization reaction Methods 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000000921 elemental analysis Methods 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 150000003512 tertiary amines Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DTFBBVDDPVULMK-UHFFFAOYSA-N 2-(aminomethylidene)propanedioic acid Chemical class NC=C(C(O)=O)C(O)=O DTFBBVDDPVULMK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical group O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
- MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 description 1
- VCVRNVYZNFWSOU-UHFFFAOYSA-N 2-chloro-5-methyl-4-nitrophenol Chemical compound CC1=CC(O)=C(Cl)C=C1[N+]([O-])=O VCVRNVYZNFWSOU-UHFFFAOYSA-N 0.000 description 1
- IJOQZZPMNWKYGI-UHFFFAOYSA-N 8-chloro-5-methyl-6-nitro-4H-1,3-benzodioxine Chemical compound CC1=C(C=C(C=2OCOCC21)Cl)[N+](=O)[O-] IJOQZZPMNWKYGI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241001104043 Syringa Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 125000003963 dichloro group Chemical class Cl* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furnace Details (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7028912A FR2101004B2 (enrdf_load_stackoverflow) | 1970-08-05 | 1970-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2139212A1 true DE2139212A1 (de) | 1972-02-10 |
Family
ID=9059833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712139212 Pending DE2139212A1 (de) | 1970-08-05 | 1971-08-05 | (Oxo-9 dihydro-6,9 4 H dioxino eckige Klammer auf 4,5-g eckige Klammer zu chinolyl-8)-carbonsäuren und ihre Isomeren |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE770708A (enrdf_load_stackoverflow) |
| CH (1) | CH529166A (enrdf_load_stackoverflow) |
| DE (1) | DE2139212A1 (enrdf_load_stackoverflow) |
| DK (1) | DK130000B (enrdf_load_stackoverflow) |
| FR (1) | FR2101004B2 (enrdf_load_stackoverflow) |
| GB (2) | GB1348259A (enrdf_load_stackoverflow) |
| NO (1) | NO136048C (enrdf_load_stackoverflow) |
| SE (1) | SE380263B (enrdf_load_stackoverflow) |
| SU (1) | SU425395A3 (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5443000B2 (enrdf_load_stackoverflow) * | 1972-07-14 | 1979-12-17 | ||
| MX2012011386A (es) | 2010-04-02 | 2012-11-29 | Senomyx Inc | Modificador del sabor dulce. |
| PH12014500184A1 (en) | 2011-08-12 | 2014-03-24 | Firmenich Incorporated | Sweet flavor modifier |
| CA2963901A1 (en) | 2014-11-07 | 2016-05-12 | Senomyx, Inc. | Substituted 4-amino-5-(cyclohexyloxy)quinoline-3-carboxylic acids as sweet flavor modifiers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH512887A (de) * | 1967-12-21 | 1971-09-30 | Ciba Geigy Ag | Neues Beifuttermittel |
-
1970
- 1970-08-05 FR FR7028912A patent/FR2101004B2/fr not_active Expired
-
1971
- 1971-07-30 BE BE770708A patent/BE770708A/xx unknown
- 1971-08-04 DK DK381571A patent/DK130000B/da unknown
- 1971-08-04 CH CH1150071A patent/CH529166A/fr not_active IP Right Cessation
- 1971-08-04 NO NO292071A patent/NO136048C/no unknown
- 1971-08-04 SE SE1001371A patent/SE380263B/xx unknown
- 1971-08-05 GB GB3037471A patent/GB1348259A/en not_active Expired
- 1971-08-05 DE DE19712139212 patent/DE2139212A1/de active Pending
- 1971-08-05 GB GB3684671A patent/GB1348258A/en not_active Expired
- 1971-08-05 SU SU1692116A patent/SU425395A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1348259A (en) | 1974-03-13 |
| FR2101004B2 (enrdf_load_stackoverflow) | 1974-02-01 |
| SE380263B (sv) | 1975-11-03 |
| BE770708A (fr) | 1971-12-01 |
| GB1348258A (en) | 1974-03-13 |
| NO136048C (no) | 1977-07-13 |
| NO136048B (enrdf_load_stackoverflow) | 1977-04-04 |
| SU425395A3 (ru) | 1974-04-25 |
| DK130000B (da) | 1974-12-09 |
| FR2101004A2 (enrdf_load_stackoverflow) | 1972-03-31 |
| CH529166A (fr) | 1972-10-15 |
| DK130000C (enrdf_load_stackoverflow) | 1975-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |